Potassium Carbonate → HCID 59402898, compound

HRID 415666Notes

Reaction equation

[CH3:1][O:2][C:3]([C:5]1[S:9][C:8]([CH2:10]Br)=[N:7][C:6]=1[C:12]1[CH:17]=[CH:16][C:15]([O:18][CH3:19])=[CH:14][CH:13]=1)=[O:4].[F:20][C:21]1[C:29]([OH:30])=[CH:28][CH:27]=[C:26]([F:31])[C:22]=1[C:23]([NH2:25])=[O:24].C(=O)([O-])[O-].[K+].[K+]>CN(C=O)C>[CH3:1][O:2][C:3]([C:5]1[S:9][C:8]([CH2:10][O:30][C:29]2[CH:28]=[CH:27][C:26]([F:31])=[C:22]([C:23](=[O:24])[NH2:25])[C:21]=2[F:20])=[N:7][C:6]=1[C:12]1[CH:17]=[CH:16][C:15]([O:18][CH3:19])=[CH:14][CH:13]=1)=[O:4]

Participants

Conditions

Temperature: 25 °C

Procedure

To a solution of 2-Bromomethyl-4-(4-methoxy-phenyl)-thiazole-5-carboxylic acid methyl ester (0.05 g, 0.14 mmol) in 2 ml of anhydrous DMF was added 2,6-Difluoro-3-hydroxy-benzamide (0.025 g, 0.14 mmol) and potassium carbonate (0.07 g, 0.50 mmol). The reaction mixture was stirred at 25° C. for 24 h under nitrogen atmosphere. The reaction mixture was evaporated to dryness under reduced pressure and the residue was purified by column chromatography on silica (60-120 M) using ethyl acetate/hexane (50:50) as the eluent to provide the title compound as white solid (0.025 g, 40%). 1H NMR (DMSO-d6, 400 MHz): δ 3.76 (s, 3H), 3.81 (s, 3H), 5.60 (s, 2H), 7.01 (d, J=8.40 Hz, 2H), 7.12 (m, 1H), 7.41 (m, 1H), 7.74 (d, J=8.40 Hz, 2H), 7.90 (br s, 1H) and 8.18 (br s, 1H). MS ES+ (435.06), HPLC (method I) Rt=15.86 min.

Workup

customThe reaction mixture was evaporated to dryness under reduced pressure
customthe residue was purified by column chromatography on silica (60-120 M)

Sources & evidence

ORD record: ord-7b93b97998dd4e27896b3b6a50170673
Source dataset: uspto-grants-2012_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08088791B2

Reaction notes

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